How to Go From Best Friend to Boyfriend

Written by JosephDecember 20, 2014

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The fine line between “boy” and “friend” is much wider than any of us think, especially in the gay community. So many gay guys are afraid of being upfront about our feelings, which gets you nowhere. Trust me. It’s tough being considered your crush’s best friend. The role is easy to take on because you’ve […]

The fine line between “boy” and “friend” is much wider than any of us think, especially in the gay community. So many gay guys are afraid of being upfront about our feelings, which gets you nowhere. Trust me.
It’s tough being considered your crush’s best friend. The role is easy to take on because you’ve probably done it all your life, but the thought of transitioning into the boyfriend category terrifies you to pieces. I’m here to tell you it isn’t as difficult as you think. Everyone wants their boyfriend to be their best friend, right? All you have to do is show him it’s possible. Here are a few ways:

Stop Talking About Other Guys In Front of Him
This includes horny cat calling when you’re both out in the gayborhoods or anywhere else. The trick is making him feel like you’re paying attention to him, and not the sexy runner in short shorts running by the café you’re sitting at. It’s all about engagement. When you engage with him, he feels like you’re doing more than just “hanging out.” You’re bonding, connecting, and enjoying each other’s company outside of the normal friend zone. Not to mention, it sends a message that you’re emotionally available. Trust me, it’ll be much harder to plant a romantic seed when he’s always catching you eyeing the guy behind him. 
Defend Him When It’s Necessary
Let’s say you’re hanging out with a group of friends and someone pokes fun at the shirt he’s wearing. A best friend would join in on the fun – it’s all harmless right? Well, if you want to take it a step further you should always come to his defense and say something like, “Aw. Stop. I think it’s cute” or pull him aside and say, “Haha. Don’t listen to these a$$holes. You look awesome.” Let him know you have his back and he’ll unconsciously begin to feel more open around you, which will welcome opportunities for intimate thoughts.
Start Asking Personal Questions
I’ve found one of the main reasons why guys considered me a best friend was because I never made an effort to enter his personal space. You should always consider his space no matter what, but there’s a fine line between being cautious and being scared. When we’re asked person questions, we tend to answer them in a personal way, so what would happen if you take a step further?
Let’s say a friend asks you “How was your weekend?” or “What are you up to today?” These are bland scenarios welcoming a generic response. If they took it up a notch with questions like, “Who were you with?” or “Did you have fun?” or “We totally should go there, what do you say?” you’re forced to respond in a personal way. Though they’re small innuendos, they’re non-obvious ways to try and inch yourself into starting a new kind of dialogue.
Don’t Tell The Entire World About It
I’ve seen countless of men heartbroken because they’ve told their network of friends how much they liked so-and-so. Doing this always makes a fool out of him. He’s going to be the one out of the loop, and secrets like this will never stay closeted for long. He’ll eventually find out from someone and he probably will feel awkward because everyone knew except him. This isn’t junior high. There’s no need to make your crush the center of everyone else’s world.
Confiding in a person about how much you adore him is enough. Make sure it’s someone you trust won’t spread it around like wildfire. You never know what will happen in the next three months. You might lose your feelings for him pretty soon and then it would have been a wasted effort. Keep it under wraps for now and never let there be an elephant in the room whenever your group of friends are together. It’s not fair for you and definitely isn’t fair for him.
Keep An Air of Mystery
I get it. You’re best friends and you share everything with each other, but now is a good time to start filtering some of it out. An interesting thing happens when there is an air of mystery. Human beings are natural problem solvers, so much of our mental cravings come from wanting to be in the “know.” This unconsciously brings us closer to whomever we’re targeting at the time. He doesn’t need to know every detail about your daily life. It’ll be much more gratifying for him when he finds out your obsession with Billy Joel, your secret spoon collection, or even the secret spot you like to drive to when you’re stressed. Keep some secrets for yourself so when you open up to him, it makes them all the more special.
Stop Playing Hard To Get
Playing hard to get looks good on paper, but only with people you aren’t as close with. Your best friend is a whole other story. Pretending you’re uninterested or trying to look unaffected by his presence will not make him come to you. It will probably get him ticked off. He’s not just some shmuck you met at a party.
Relax a bit and stop trying to play games to win his affection. You already have it. If you want to get him to see you as something more you should work at tightening the bond, not working the field. It’s a little too late for that – you know each other too well already. Upgrade your attitude and start building a new foundation on top of the one you have. Change his outlook on you without changing his opinion.
Plan One-on-One Time
A best friend hangs out with other best friends, but boyfriends go out together alone. Try and make this a new habit. Not that group outings and parties of mutual friends are bad things necessarily, but too much of them will get you both used to the relationship that currently exists. Eventually it will be hard to imagine anything deeper. Lunches, jogs, happy hours, theater, and coffee are all small gestures, but in the grand scheme of things they tend to be quite lucrative. You’d be surprised what can happen when it’s just the two of you.
Plant The Seed & Test The Waters
There are plenty of ways to drop hints without feeling awkward or invasive, and most of the time you can do them without him knowing it. Sayings things like “You look handsome today” or “I really respect what you did” or “You’re very noble” or “You’re so nice” or “You’re the eye candy tonight” or “You’re the best” allows you to see his reaction and go from there. Comments that boost his confidence will unconsciously make him more comfortable around you, not to mention they give him an idea on how you feel about him. The rest might happen naturally.
Nonchalant Touching
Eek! I know, right? Even for gay guys it can be awkward to touch each other in an intimate way. It’s much easier for women. We have a man complex about ourselves and we’re too scared to break it down. But if they can do it in Europe, why can’t we? The slightest touch sends signals all the way to our brain, so the more touching the better.
There are casual ways of touching him without making him think anything’s changed. The secret is makinghim be the one to start touching rather than you. This way, in his mind, he’ll think he’s the one initiating it. Skip the fist pump and start thinking about body contact. Hugging, playful pushing, eye contact, a harmless game of thumb war, drunk palm readings, and shoulder rubs are a lot easier to initiate than you think. Trust me on this.
Stop Procrastinating & Make an Effort
Our greatest fear is that our entire friendship will be ruined if we let the cat out of the bag. We’re left with constant paranoia. The “friendship” is always at the top of our worry. Everything is surrounding the sake of the relationship, but never should you let this fuel your decision to at least see if it’s possible.
My philosophy is you’ll never know until you try. The only feeling worse than the loss of a friend is the regret of never having tried at all. Start planning outings together – wine & TV marathons, weekly happy hour traditions, or coffee shop meet ups. Find something that works and make it “your time.” Start the transition sooner rather than later, trust me, you don’t want to lose precious time living inside your head.
Have Balls When An Opportunity Finally Arrives
Don’t lose your confidence when the time comes to tell him the truth. If he starts to realize your attraction and welcomes it, don’t crawl back into your shell. I know how easy it is. The world inside our imagination is much more comfortable than real life. When everything happens exactly how we pictured it, we have the potential of losing our cool and wanting to run away.
If he ends up asking you if you like him, don’t try and pretend like you don’t. If there’s an opportunity for you to kiss, though it might feel weird at first, don’t be ashamed in at least trying. Whenever he smiles at you in an obviously romantic way, never ignore it. The last thing you want him to think is that you’ve been leading him on. You want him to feel attached to you, so give it back to him when it’s received and be ecstatic that it finally happened.

Have you found the right one, or are you still searching?
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